How fatty acids of different chain length enter and leave cells by free diffusion

Zakim, 1996, Fatty acids enter cells by simple diffusion, Proc. Soc. Exp. Biol. Med., 212, 5, 10.3181/00379727-212-43986 Nardi, 1999 Hamilton, 2003, Fast flip-flop of cholesterol and fatty acids in membranes: implications for membrane transport proteins, Curr. Opin. Lipidol., 14, 263, 10.1097/00041433-200306000-00006 Hamilton, 1999, How are free fatty acids transported in membranes? Is it by proteins or by free diffusion through the lipids?, Diabetes, 48, 2255, 10.2337/diabetes.48.12.2255 Hamilton, 2001, Fatty acid transport. The diffusion mechanism in model and biological membranes, J. Mol. Neurosci., 16, 99, 10.1385/JMN:16:2-3:99 Bojesen, 2002, Studies of membrane transport mechanism of long-chain fatty acids in human erythrocytes, Rec. Res. Devel. Membr. Biol., 1, 33 Kleinfeld, 2000, Lipid phase fatty acid flip-flop, is it fast enough for cellular transport?, J. Membr. Biol., 175, 79, 10.1007/s002320001056 Zakim, 2000, Thermodynamics of fatty acid transfer, J. Membr. Biol., 176, 101, 10.1007/s002320001080 Glatz, 2001, Unravelling the significance of cellular fatty acid-binding proteins, Curr. Opin. Lipidol., 12, 267, 10.1097/00041433-200106000-00005 van der Vusse, 2002, Critical steps in cellular fatty acid uptake and utilization, Mol. Cell Biochem., 239, 9, 10.1023/A:1020538119691 Al-Awqati, 1999, One hundred years of membrane permeability: does Overton still rule?, Nat. Cell Biol., 1, E201, 10.1038/70230 Stein, 1986 Hamilton, 1986, Transfer of oleic acid between albumin and phospholipid vesicles, Proc. Natl. Acad. Sci. USA, 83, 82, 10.1073/pnas.83.1.82 McLaughlin, 1980, Transport of protons across membranes by weak acids, Physiol. Rev., 60, 825, 10.1152/physrev.1980.60.3.825 Gutknecht, 1988, Proton conductance caused by long-chain fatty acids in phospholipid bilayer membranes, J. Membr. Biol., 106, 83, 10.1007/BF01871769 Dietschy, 1978, Lipid movement across biological membranes, 1 Sallee, 1973, Determinants of intestinal mucosal uptake of short- and medium-chain fatty acids and alcohols, J. Lipid Res., 14, 475, 10.1016/S0022-2275(20)36881-4 Westergaard, 1974, Delineation of the dimensions and permeability characteristics of the two major diffusion barriers to passive mucosal uptake in the rabbit intestine, J. Clin. Invest., 54, 718, 10.1172/JCI107810 Rosen, 1964, Diffusion of weak acids across the toad bladder, J. Gen. Physiol., 48, 379, 10.1085/jgp.48.2.379 Sherrill, 1975, Permeabiliy characteristics of the adipocyte cell membrane and partitioning characteristics of the adipocyte triglyceride core, J. Membr. Biol., 23, 367, 10.1007/BF01870258 Knittle, 1965, Effect of chain length on rates of uptake of free fatty acids during in vitro incubations of rat adipose tissue, J. Lipid Res., 6, 565, 10.1016/S0022-2275(20)39623-1 Walter, 1984, Monocarboxylic acid permeation through lipid bilayer membranes, J. Membr. Biol., 77, 255, 10.1007/BF01870573 Evtodienko, 1996, Effect of the alkyl chain length of monocarboxylic acid on the permeation through bilayer lipid membranes, Biochim. Biophys. Acta, 1281, 245, 10.1016/0005-2736(96)00023-5 Prestegard, 1979, Nuclear magnetic resonance determinations of permeation coefficients for maleic acid in phospholipid vesicles, Biophys. J., 26, 575, 10.1016/S0006-3495(79)85272-8 Cramer, 1977, NMR studies of pH-induced transport of carboxylic acids across phospholipid vesicle membranes, Biochem. Biophys. Res. Commun., 75, 295, 10.1016/0006-291X(77)91042-7 Evtodienko, 1999, Permeation of dicarboxylic acids with different terminal position of two carboxylic groups through planar bilayer lipid membranes, Biochim. Biophys. Acta, 1420, 95, 10.1016/S0005-2736(99)00095-4 Richieri, 1993, Interactions of long-chain fatty acids and albumin: determination of free fatty acid levels using the fluorescent probe ADIFAB, Biochemistry, 32, 7574, 10.1021/bi00080a032 Dancis, 1974, Transfer across perfused human placenta. 3. Effect of chain length on transfer of free fatty acids, Pediatr. Res., 8, 796, 10.1203/00006450-197409000-00004 Dancis, 1976, Transfer across perfused human placenta. IV. Effect of protein binding on free fatty acids, Pediatr. Res., 10, 5, 10.1203/00006450-197601000-00002 Cooper, 1987, A physical-chemical model for cellular uptake of fatty acids: prediction of intracellular pool sizes, Biochemistry, 26, 5890, 10.1021/bi00392a047 Noy, 1986, Physical-chemical model for the entry of water-insoluble compounds into cells. Studies of fatty acid uptake by the liver, Biochemistry, 25, 2013, 10.1021/bi00356a027 Zakim, 1987, The uptake of fatty acids by the liver, Trans. Am. Clin. Climatol. Assoc., 99, 41 Simpson, 1974, Partition of fatty acids, J. Lipid Res., 15, 415, 10.1016/S0022-2275(20)36790-0 Spector, 1971, Analysis of long-chain free fatty acid binding to bovine serum albumin by determination of stepwise equilibrium constants, Biochemistry, 10, 3229, 10.1021/bi00793a011 Kamp, 2003, Rapid flip-flop of oleic acid across the plasma membrane of adipocytes, J. Biol. Chem., 278, 7988, 10.1074/jbc.M206648200 Richieri, 1995, Thermodynamics of fatty acid binding to fatty acid-binding proteins and fatty acid partition between water and membranes measured using the fluorescent probe ADIFAB, J. Biol. Chem., 270, 15076, 10.1074/jbc.270.25.15076 Brunaldi, 2005, Fatty acid flip-flop and proton transport determined by short-circuit current in planar bilayers, J. Lipid Res., 46, 245, 10.1194/jlr.M400155-JLR200 Romano-Fontes, 2000, Fatty acid transport across lipid bilayer planar membranes, Lipids, 35, 31, 10.1007/s11745-000-0491-4 Gawrisch, 2003, The structure of DHA in phospholipid membranes, Lipids, 38, 445, 10.1007/s11745-003-1082-0 Marti, 2004, Transition path sampling study of flip-flop transitions in model lipid bilayer membranes, Phys. Rev. E Stat. Nonlin. Soft Matter Phys., 69, 061918, 10.1103/PhysRevE.69.061918 Kamp, 1992, pH Gradients across phospholipid membranes caused by fast flip-flop of fatty acids, Proc. Natl. Acad. Sci. USA, 85, 11367, 10.1073/pnas.89.23.11367 Kamp, 1993, Movement of fatty acids, fatty acid analogues, and bile acids across phospholipid bilayers, Biochemistry, 32, 11074, 10.1021/bi00092a017 Kamp, 1995, Fatty acid flip-flop in phospholipid bilayers is extremely fast, Biochemistry, 34, 11928, 10.1021/bi00037a034 Hamilton, 2002, Mechanism of cellular uptake of long-chain fatty acids: Do we need cellular proteins?, Mol. Cell Biochem., 239, 17, 10.1023/A:1020542220599 Guo, 2006, Fatty acid transport and metabolism in HepG2 cells, Am. J. Physiol. Gastrointest. Liver Physiol., 290, G528, 10.1152/ajpgi.00386.2005 Zhang, 1996, Dissociation of long and very long chain fatty acids from phospholipid bilayers, Biochemistry, 35, 16055, 10.1021/bi961685b Massey, 1997, Spontaneous transfer of monoacyl amphiphiles between lipid and protein surfaces, Biophys. J., 72, 1732, 10.1016/S0006-3495(97)78819-2 Cupp, 2004, Fatty acid-albumin complexes and the determination of the transport of long chain free fatty acids across membranes, Biochemistry, 43, 4473, 10.1021/bi036335l Kleinfeld, 1997, Transport of long-chain native fatty acids across lipid bilayer membranes indicates that transbilayer flip-flop is rate limiting, Biochemistry, 36, 14146, 10.1021/bi971440e King, 2004, From structure to disease: the evolving tale of aquaporin biology, Nat. Rev. Mol. Cell Biol., 5, 687, 10.1038/nrm1469 Fenton, 2006, UT-A urea transporter promoter, UT-Alpha, targets principal cells of the renal inner medullary collecting duct, Am. J. Physiol. Renal Physiol., 290, F188, 10.1152/ajprenal.00285.2005 MacDougald, 2005, Obesity and metabolic perturbations after loss of aquaporin 7, the adipose glycerol transporter, Proc. Natl. Acad. Sci. USA, 102, 10759, 10.1073/pnas.0504965102 Chu, 1995, An Na+-independent short-chain fatty acid transporter contributes to intracellular pH regulation in murine colonocytes, J. Gen. Physiol., 105, 589, 10.1085/jgp.105.5.589 Small, 1997, Point mutations in the ileal bile salt transporter cause leaks in the enterohepatic circulation leading to severe chronic diarrhea and malabsorption, J. Clin. Invest., 99, 1807, 10.1172/JCI119345 Alonso de la Torre, 1992, Carrier-mediated beta-D-hydroxybutyrate transport in brush-border membrane vesicles from rat placenta, Pediatr. Res., 32, 317, 10.1203/00006450-199209000-00014 Latruffe, 1987, Transport of D-beta-hydroxybutyrate across rat liver mitochondrial membranes, Comp. Biochem. Physiol. B, 88, 797, 10.1016/0305-0491(87)90246-X Hamilton, 2004, Fatty acid interactions with proteins: what X-ray crystal and NMR solution structures tell us, Prog. Lipid Res., 43, 177, 10.1016/j.plipres.2003.09.002 Simard, 2005, Locating high-affinity fatty acid-binding sites on albumin by X-ray crystallography and NMR spectroscopy, Proc. Natl. Acad. Sci. USA, 102, 17958, 10.1073/pnas.0506440102 Civelek, 1996, Intracellular pH in adipocytes: effects of free fatty acid diffusion across the plasma membrane, lipolytic agonists, and insulin, Proc. Natl. Acad. Sci. USA, 93, 10139, 10.1073/pnas.93.19.10139 Katchalsky, 1965 Musters, 2006, Computational evidence for protein-mediated fatty acid transport across the sarcolemma, Biochem. J., 393, 669, 10.1042/BJ20050869 Demant, 2002, Stopped-flow kinetic analysis of long-chain fatty acid dissociation from bovine serum albumin, Biochem. J., 363, 809, 10.1042/0264-6021:3630809 Bojesen, 1996, Albumin binding of long-chain fatty acids: thermodynamics and kinetics, J. Biol. Chem., 100, 17981 Ibrahimi, 2002, Role of CD36 in membrane transport of long-chain fatty acids, Curr. Opin. Clin. Nutr. Metab. Care, 5, 139, 10.1097/00075197-200203000-00004 Stahl, 2002, Insulin causes fatty acid transport protein translocation and enhanced fatty acid uptake in adipocytes, Dev. Cell, 2, 477, 10.1016/S1534-5807(02)00143-0 Kim, 2004, Inactivation of fatty acid transport protein 1 prevents fat-induced insulin resistance in skeletal muscle, J. Clin. Invest., 113, 756, 10.1172/JCI200418917 Hirsch, 1998, A family of fatty acid transporters conserved from mycobacterium to man, Proc. Natl. Acad. Sci. USA, 95, 8625, 10.1073/pnas.95.15.8625 van den Berg, 2004, Crystal structure of the long-chain fatty acid transporter FadL, Science, 304, 1506, 10.1126/science.1097524 Ek, 1997, Fatty acid binding proteins reduce 15-lipoxygenase-induced oxygenation of linoleic acid and arachidonic acid, Biochim. Biophys. Acta, 1346, 75, 10.1016/S0005-2760(97)00021-0 Pohl, 1998, The size of the unstirred layer as a function of the solute diffusion coefficient, Biophys. J., 75, 1403, 10.1016/S0006-3495(98)74058-5 Antonenko, 1993, Weak acid transport across bilayer lipid membrane in the presence of buffers. Theoretical and experimental pH profiles in the unstirred layers, Biophys. J., 64, 1701, 10.1016/S0006-3495(93)81542-X Barta, 2000, Facilitated diffusion and membrane permeation of fatty acid in albumin solutions, Ann. Biomed. Eng., 28, 331, 10.1114/1.274 Hamilton, 1995, Studies of minor lipid constituents of membranes by hight resolution and solid state 13C NMR spectroscopy: interactions with phospholipid bilayers and transport proteins, 117 Petitpas, 2001, Crystal structures of human serum albumin complexed with monounsaturated and polyunsaturated fatty acids, J. Mol. Biol., 314, 955, 10.1006/jmbi.2000.5208 Pownall, 2003, Energy translocation across cell membranes and membrane models, Acta Physiol. Scand., 178, 357, 10.1046/j.1365-201X.2003.01154.x Haggarty, 1997, Long-chain polyunsaturated fatty acid transport across the perfused human placenta, Placenta, 18, 635, 10.1016/S0143-4004(97)90004-7 Larque, 2003, In vivo investigation of the placental transfer of (13)C-labeled fatty acids in humans, J. Lipid Res., 44, 49, 10.1194/jlr.M200067-JLR200 Schaffer, 1994, Expression cloning and characterization of a novel adipocyte long chain fatty acid transport protein, Cell, 79, 427, 10.1016/0092-8674(94)90252-6 Watkins, 1999, Human very long-chain acyl-CoA synthetase and two human homologs: initial characterization and relationship to fatty acid transport protein, Prostaglandins Leukot. Essent. Fatty Acids, 60, 323, 10.1016/S0952-3278(99)80007-6 Pei, 2004, Mouse very long-chain Acyl-CoA synthetase 3/fatty acid transport protein 3 catalyzes fatty acid activation but not fatty acid transport in MA-10 cells, J. Biol. Chem., 279, 54454, 10.1074/jbc.M410091200 Meshulam, 2006, Role of caveolin-1 and cholesterol in transmembrane Fatty Acid movement, Biochemistry, 45, 2882, 10.1021/bi051999b Gutknecht, 1987, Proton/hydroxide conductance and permeability through phospholipid bilayer membranes, Proc. Natl. Acad. Sci. USA, 84, 6443, 10.1073/pnas.84.18.6443 Orbach, 1980, The nonelectrolyte permeability of planar lipid bilayer membranes, J. Gen. Physiol., 75, 427, 10.1085/jgp.75.4.427 Deamer, 1986, Permeability of lipid bilayers to water and ionic solutes, Chem. Phys. Lipids, 40, 167, 10.1016/0009-3084(86)90069-1 Reeves, 1970, Water permeability of phospholipid vesicles, J. Membr. Biol., 3, 123, 10.1007/BF01868011 Alger, 1979, Nuclear magnetic resonance study of acetic acid permeation of large unilamellar vesicle membranes, Biophys. J., 28, 1, 10.1016/S0006-3495(79)85154-1